Don't Underestimate Your Opponent

A couple of weekends ago, I went to my old friend Eliot’s house, which I was really looking forward to as I’ve rarely seen him over the past 30 years. You know how that goes. One minute you’re just graduating from high school, ready to take the world by storm, and the next you’re looking at your retirement, wondering where all the years went.

Anyway, while I was there, Eliot asked me if I wanted to play a game of backgammon with him. But first, he questioned whether or not I was any good at it. Specifically, he wanted to know if I would play him for $100 a point. Instantly I said no, and not because I was necessarily better or worse than him (that part I didn’t know), but because I don’t like to make blind bets.

That’s when Eliot came up with a different bet. If we played and I won, I would take his place in an upcoming backgammon tournament in Monte Carlo. And if I lost, I had to write a blog about my experience. (Since you’re reading this, then it’s pretty clear how the game ended, but it wasn’t quite as clear a win as it may seem.)

During our game, which involved the winner being the first person to reach 11 points, Eliot taught me the intricacies of backgammon. He must have been a pretty good teacher too because it came down to three rolls of the dice during our final game.

In complete transparency, Eliot was much better than I, way more experienced at mastering the game. I know that if we would have played 100 games that weekend, he would’ve won at least 90 of them. But this one time, I could have actually won. I could have taken his ticket to Monte Carlo and his spot in the tournament, mainly because of luck.

This reminded me that, while being skilled is critical to excelling in life, whether personally or professionally, luck plays a part as well. That’s why it’s important to not get too over-confident. There’s always that chance that you can be taken down by someone with less experience or less knowledge, which means that staying humble and not “betting it all” is often the best approach.

Take the time to get to know your opponent. In this case, Eliot clearly was more skilled at backgammon than I and expected to win because of it. But sometimes life tosses us a curve ball, so we must be prepared.

Sure, I wound up losing, but it wasn’t until right at the end. Had those three rolls gone my way, I’d be sitting on a plane as we speak, ready to test my luck again, hoping to walk away with even more unskilled wins. Luckily for Eliot, I wasn’t.

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